“Dinner and Drinks? Or Whiskey and a walk?”

Date #13

Push-ups – 40 (Day 13)

Push-ups – 75 (Day 24)

“Dinner and Drinks? Or Whiskey and a walk?”


This is what it’s all about. Tonight’s the night. The rare night I don’t have my daughter. I have the entire night to do whatever I want. What’s a girl to do? A part of me wants to stay home in sweatpants, do a little writing, maybe watch a movie and sleep. But it’s time to take myself out to paint the town and mix it up! I stood in my bedroom and imagined I was being asked on a normal date. If I’m going to date myself, there must be the classic go out for a drink and dinner date as part of my 30 dates.


“Anna, would you like to do something tonight? Go grab a drink somewhere and eat dinner?”

“Sure!” I replied.

“What do you want to do? Where do you want to go?”

Shit balls.

This is the problem! I began to sift through my brain catalog and think. It feels like I’m searching through the library catalog drawers and am the Dewey Decimal System to locate restaurants. I try to picture all the restaurants and think about where I want to go. If I could go anywhere and eat whatever I wanted to, where would I go? I don’t know where to go anymore! I use to, but thing are different now.


I had my time in the party scene. I was in my early 20’s and thought I was invisible like everyone else in my posse. My girlfriends and I would pull up to Whiskey Park on Howard Avenue on any given night feeling like we were Angelina Jolie and Britney Spears. We were more like lip-syncing wannabees.


Something happens when you leave the night scene and focus on different goals for your life. You think because you stopped going out, everyone else did too. I’m laughing because that’s not true, but it can feel like that.


People call this time of their life, “the good ‘ol days.” But I believe the “best times of my life” are soon to come.


The Date.


Where do you want to go!?


The truth is, I don’t know. And the more I think about it, the more I wonder if I just don’t care. I like to eat and I like to have a cocktail from time to time. I want to go out to dinner, have a nice glass of wine and enjoy a great meal. As I dig more into this dating myself thing, I realize I’m not looking for someone to go out to eat with or a night out on the town. Although it’s nice to do that with my boyfriend, I can enjoy going out to eat or drinks with friends and social events. So, what am I looking for? The mundane. The downtime. Living life. I don’t need to be out and about in the night scene. Can I make the night scene exciting at home? You bet!


Nonetheless, it was date night and I wanted to put on my heals, gloss my lips red, and go out.


I texted a friend to asked, “If I wanted to take a hot girl out (giggle) for a drink with a good vibe and cool bar scene, where would I take her?”


He gave a few options, but the first one immediately caught my attention, Fly Bar & Restaurant – Tampa, FL. Perfect! I haven’t been there since my mortgage broker days and remembered they had a rooftop bar. I could see myself going there so I began getting ready for my big date.


Three hours later….


Just kidding, but I took my time getting ready and enjoyed the process. I left the house feeling great in my high-heals and headed to CVS to get some lip gloss. I have a 6-year-old who is obsessed with lip gloss, so I every time I turn around, it’s gone.


As a busy mom and businesswoman, it feels good to take some time for yourself and look your best. Yes, what’s inside and who you are as a person matters the most, but that doesn’t mean you can’t match that awesomeness on the outside. I love yoga pants, then again it’s nice to not have Lycra stuck to my butt 24/7.


I drove downtown feeling good as I listened to an Angels and Airwaves record. After parking, I walked towards Fly Bar and heard live music in the air.


My heals strutted right past the Fly Bar and towards the music. It was coming from the popular downtown bar, The Franklin Manor. Perfect! I have never been there and wanted to see what all the buzz was about. I walked in, posted up at the bar and ordered a Kettle and cran.


The sun was setting as I felt the reverberations of the acoustic guitar and as usual, the music captured my soul.


I sat there for a bit, enjoying my drink and music, but became slightly bored. What do I do? Just sit here? That’s a tough one! Even so, I didn’t want to be rude to my date so I looked at the drink menu in search for something exciting. As I scanned the drink menu, “In Harmony Old Fashion” stood out, not because of the name, but because of the $39 price tag. $39 for a drink? I was tempted to order and impress myself.


Kristian, the bartender, checked on me a few times and ended up making my experience fun. He explained the $39 drink before suggesting the $12 Smoked Irish Old Fashion, saying it would be just as impressive. Sold. It was an exciting drink! So much, I had two of them. I weigh a buck twenty and I’m not a big drinker, therefore two whiskeys hit me.


A girlfriend of mine and her friend stopped by after their networking event to join me towards the end of my date. We chatted about the hurricane aftermath and they ordered some food. The alcohol was creeping in and I had been sitting for too long. I already was soaking fresh air being at an outdoor bar, but I was ready for new scenery and was craving a walk. I knew I didn’t want to sit at a bar any longer, not to mention I was hungry!


That’s whats so cool about dating yourself, you don’t have to ask the other person if they want to leave too! You leave when YOU want to!


I was ready to walk off the whiskey. I wanted to stroll through the colored lights that shine throughout our downtown streets at night. I live in a beautiful city and I want to enjoy it!


I reached out to a friend who lived close by and asked if he would like to join me to walk off the whiskey that was starting to make me a bit chatty. He said yes, so I paid my tab, said my goodbyes and headed out for a stroll downtown.


On a prior date with myself, I learned I love being at Curtis Hixon park and sitting on those deck things, so it was natural to walk towards the park. We crossed over the lit-up water fountains and laughed about the fact I was tipsy. I was giggly as I sat down on the deck and looked over at The University of Tampa before laying down. I felt my inner child-like spirit take over as I laid back and gazed up at the untidiness of the stars. There’s beauty in what looks like disorder. Stars everywhere, shining bright in what looks like imperfect patterns. When in reality, those messy stars are constellations forming beautiful patterns and asterisms if you learn to see beyond. The beauty in the imperfect is to see what’s beyond and what’s really there. When we see all the intricacies in someone and know who we are, connection is made and love can grow.


I don’t encourage drinking, nor is it an interest to me unless it’s about fun celebrating or relaxing. For me, there is something fun about having a couple drinks and letting go. It’s the feeling of relaxation to release all my thoughts and anxieties to just let go. However, the desire amongst most of us, including myself, is to have practices in place within ourselves, knowing who we are enough to let go and breathe without alcohol. Everyone has the right to feel freedom and experience joy without “needing” alcohol to do that. 😊 There are many healthy ways to relax and release anxieties such as meditation, prayer, mindfulness, exercise, connecting with others, playing, being still with the earth, yoga, etc. Find your way to breathe!

Engaged in the view of the stars, we laid there talking about why sitting at the park makes me happy. We got up to continue our walk and wondered over to the railroad tracks to view a large city mural painted on the side of a parking garage.


These dates with myself are all about pausing to not only see what I love, but to also pause and see the world. I’ve walked past the mural many times, but never really SAW it. Tonight I did. Hopefully, I’ll still remember seeing it in the morning. 😉 I’m kidding!


Conclusion –

I enjoy getting dressed up to go out for a night on the town and I apparently like fun whiskey drinks. The circumstances and why I’m going out matters to me and it also has a time limit. Sitting at the bar is not my favorite thing to do but I do like to sit and enjoy a nice drink outside or at an event.


Tonight was a reminder that it’s the company you surround yourself with that makes going out enjoyable, not the perfect place. When my friends joined me at the bar, it became more about us instead of where we were. I can get so caught up in thinking about the perfect atmosphere and place, that I forget about the importance of who I am with. There was no perfect walking route as we walked the streets and there wasn’t a perfect place to sit and look at the stars. The perfection was in the bliss of the moment. The enjoyment comes from being still with myself and also enjoying those moments with someone else.


Until tomorrow….or the next day….or the next….


On that note, I would like to change my “30 dates in 30 days” to “30 dates with yourself.” In true transparency, it was tough trying to take myself on a date every day, even if it was small. In addition to the hurricane setback, I realize life happens and as much as we want to implement something new into our lives, it doesn’t always happen as easy as we’d like it to. The goal is to not give up and commit to picking up where you left off.


I won’t give up on my 30 dates with myself and I promise to finish this experiment of finding the best way to have 30 dates with yourself!

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